Palladium-catalyzed borylation of 4-chlorotoluene^a.

Entry	Boron reagent	Catalyst	Ligand	Time (h)	Yieldb (%)
1	B2pin2	Pd2dba3	XPhos	10	0, 84c
2	H-Bpin	Pd2dba3	XPhos	10	0d, 45c,d
3	B2pin2	PdCl2(dppf)2	—	10	0c,e
4	B2pin2	Pd(OAc)2	XPhos	10	0, 72c
5	H-Bpin	Pd(OAc)2	XPhos	10	0d, 37c,d
6	B2pin2	Pd(OAc)2	SPhos	48	38
7	B2pin2	XPhos-Pd-G2	XPhos	1.0	17
8	H-Bpin	XPhos-Pd-G2	XPhos	1.0	11d

^aReaction conditions: 1a (1.0 equiv.), boron reagent (3.0 equiv.), KOAc (3.0 equiv.), dioxane (0.5 M), cat. [Pd]/ligand = 1 : 2, RT.

^bIsolated yield.

^cSealed tube, 110 °C.

^dEt₃N as solvent.

^eDMF as solvent.